ES2273864T3 - Nueva formulacion en aerosol que contiene una molecula fluorada polar. - Google Patents

Info

Publication number

ES2273864T3

ES2273864T3 ES01952071T ES01952071T ES2273864T3 ES 2273864 T3 ES2273864 T3 ES 2273864T3 ES 01952071 T ES01952071 T ES 01952071T ES 01952071 T ES01952071 T ES 01952071T ES 2273864 T3 ES2273864 T3 ES 2273864T3

Authority

ES

Spain

Prior art keywords

perfluoro

methyl

ethyl

peg

hfa

Prior art date

2000-07-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims description 104
• 238000009472 formulation Methods 0.000 title claims description 90
• 239000000443 aerosol Substances 0.000 title claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 41
• 239000003814 drug Substances 0.000 claims abstract description 37
• 229940079593 drug Drugs 0.000 claims abstract description 35
• 239000003380 propellant Substances 0.000 claims abstract description 30
• 239000007788 liquid Substances 0.000 claims abstract description 11
• GRJRKPMIRMSBNK-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRJRKPMIRMSBNK-UHFFFAOYSA-N 0.000 claims abstract description 8
• UQZFWRDNDBASDI-UHFFFAOYSA-N ethyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tricosafluorododecanoate Chemical compound CCOC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UQZFWRDNDBASDI-UHFFFAOYSA-N 0.000 claims abstract description 7
• ZYAMKYAPIQPWQR-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-3-methoxypropane Chemical compound COCC(F)(F)C(F)(F)F ZYAMKYAPIQPWQR-UHFFFAOYSA-N 0.000 claims abstract description 6
• HCBRSIIGBBDDCD-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-3-(1,1,2,2-tetrafluoroethoxy)propane Chemical compound FC(F)C(F)(F)COC(F)(F)C(F)F HCBRSIIGBBDDCD-UHFFFAOYSA-N 0.000 claims abstract description 6
• NWDZSYHMBYNCRO-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F NWDZSYHMBYNCRO-UHFFFAOYSA-N 0.000 claims abstract description 6
• BSXJTDJJVULBTQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BSXJTDJJVULBTQ-UHFFFAOYSA-N 0.000 claims abstract description 6
• VKRFUGHXKNNIJO-UHFFFAOYSA-N 4,4,4-trifluorobutan-1-ol Chemical compound OCCCC(F)(F)F VKRFUGHXKNNIJO-UHFFFAOYSA-N 0.000 claims abstract description 6
• QJFHNYDPNSFJMR-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QJFHNYDPNSFJMR-UHFFFAOYSA-N 0.000 claims abstract description 6
• RQUXJBKONYSFAU-UHFFFAOYSA-N n,n-diethyl-2,3,3,3-tetrafluoropropanamide Chemical compound CCN(CC)C(=O)C(F)C(F)(F)F RQUXJBKONYSFAU-UHFFFAOYSA-N 0.000 claims abstract description 6
• RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• -1 4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl Chemical group 0.000 claims description 50
• YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims description 46
• 229960004436 budesonide Drugs 0.000 claims description 33
• VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 25
• LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical group FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 21
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 19
• 239000008249 pharmaceutical aerosol Substances 0.000 claims description 15
• 229920001577 copolymer Polymers 0.000 claims description 13
• 229960002848 formoterol Drugs 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• ZDCRNXMZSKCKRF-UHFFFAOYSA-N tert-butyl 4-(4-bromoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Br)C=C1 ZDCRNXMZSKCKRF-UHFFFAOYSA-N 0.000 claims description 9
• BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 6
• DUTTZBRMOIAYKM-UHFFFAOYSA-N butyl 2,2,3,3,3-pentafluoropropanoate Chemical compound CCCCOC(=O)C(F)(F)C(F)(F)F DUTTZBRMOIAYKM-UHFFFAOYSA-N 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 4
• 229960000195 terbutaline Drugs 0.000 claims description 4
• IJDRCJGYWUCJTR-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-[1,1,2,3,3,3-hexafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]propoxy]propoxy]propanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F IJDRCJGYWUCJTR-UHFFFAOYSA-N 0.000 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 206010039083 rhinitis Diseases 0.000 claims description 3
• 229960002052 salbutamol Drugs 0.000 claims description 3
• LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims description 2
• PJFHZKIDENOSJB-UHFFFAOYSA-N Budesonide/formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1.C1CC2=CC(=O)C=CC2(C)C2C1C1CC3OC(CCC)OC3(C(=O)CO)C1(C)CC2O PJFHZKIDENOSJB-UHFFFAOYSA-N 0.000 claims description 2
• 229960001022 fenoterol Drugs 0.000 claims description 2
• 239000004811 fluoropolymer Substances 0.000 claims description 2
• 229920002313 fluoropolymer Polymers 0.000 claims description 2
• YXOKBHUPEBNZOG-UHFFFAOYSA-N hydron;4-hydroxy-7-[2-[2-[3-(2-phenylethoxy)propylsulfonyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one;chloride Chemical compound Cl.C1=2SC(=O)NC=2C(O)=CC=C1CCNCCS(=O)(=O)CCCOCCC1=CC=CC=C1 YXOKBHUPEBNZOG-UHFFFAOYSA-N 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• 229940035073 symbicort Drugs 0.000 claims description 2
• BNPSSFBOAGDEEL-UHFFFAOYSA-N albuterol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 BNPSSFBOAGDEEL-UHFFFAOYSA-N 0.000 claims 1
• 150000003904 phospholipids Chemical class 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• 239000000725 suspension Substances 0.000 description 26
• 150000001875 compounds Chemical class 0.000 description 20
• 229960003610 formoterol fumarate dihydrate Drugs 0.000 description 18
• 229960005105 terbutaline sulfate Drugs 0.000 description 16
• 239000002253 acid Chemical class 0.000 description 14
• 239000002245 particle Substances 0.000 description 14
• 229920001223 polyethylene glycol Polymers 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
• 239000006071 cream Substances 0.000 description 12
• KFVSLSTULZVNPG-UHFFFAOYSA-N terbutaline sulfate Chemical compound [O-]S([O-])(=O)=O.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1 KFVSLSTULZVNPG-UHFFFAOYSA-N 0.000 description 12
• RATSWNOMCHFQGJ-TUYNVFRMSA-N (e)-but-2-enedioic acid;n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[[(2s)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1 RATSWNOMCHFQGJ-TUYNVFRMSA-N 0.000 description 11
• 229920000858 Cyclodextrin Polymers 0.000 description 11
• 238000000034 method Methods 0.000 description 11
• 229940048053 acrylate Drugs 0.000 description 10
• 239000000523 sample Substances 0.000 description 10
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
• 238000009826 distribution Methods 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
• 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 8
• 229920003081 Povidone K 30 Polymers 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 229920003149 Eudragit® E 100 Polymers 0.000 description 7
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
• NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 7
• 238000011156 evaluation Methods 0.000 description 7
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 7
• 229920003080 Povidone K 25 Polymers 0.000 description 6
• UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 6
• 229920001427 mPEG Polymers 0.000 description 6
• 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 6
• 229920000193 polymethacrylate Polymers 0.000 description 6
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 208000004998 Abdominal Pain Diseases 0.000 description 5
• 208000002881 Colic Diseases 0.000 description 5
• 239000011521 glass Substances 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
• WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 4
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
• 229920003134 Eudragit® polymer Polymers 0.000 description 4
• 239000001116 FEMA 4028 Substances 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
• 238000013019 agitation Methods 0.000 description 4
• WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 4
• 235000011175 beta-cyclodextrine Nutrition 0.000 description 4
• 229960004853 betadex Drugs 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 4
• 229940080345 gamma-cyclodextrin Drugs 0.000 description 4
• 239000012535 impurity Substances 0.000 description 4
• JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 4
• 229960001375 lactose Drugs 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 238000005191 phase separation Methods 0.000 description 4
• XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 description 3
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
• 241000501754 Astronotus ocellatus Species 0.000 description 3
• 239000005977 Ethylene Substances 0.000 description 3
• 229920002125 Sokalan® Polymers 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
• 239000004809 Teflon Substances 0.000 description 3
• 229920006362 Teflon® Polymers 0.000 description 3
• 229910052782 aluminium Inorganic materials 0.000 description 3
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 125000004386 diacrylate group Chemical group 0.000 description 3
• 238000004090 dissolution Methods 0.000 description 3
• 238000005189 flocculation Methods 0.000 description 3
• 230000016615 flocculation Effects 0.000 description 3
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• 239000013074 reference sample Substances 0.000 description 3
• 229960004889 salicylic acid Drugs 0.000 description 3
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• 238000002604 ultrasonography Methods 0.000 description 3
• GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
• JZBQCJRCMQCPKE-UHFFFAOYSA-N 1,1,1,3,3-pentafluoro-2-(1,1,1,3,3-pentafluoropropan-2-yloxy)propane Chemical compound FC(F)C(C(F)(F)F)OC(C(F)F)C(F)(F)F JZBQCJRCMQCPKE-UHFFFAOYSA-N 0.000 description 2
• NHEKBXPLFJSSBZ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorohexane-1,6-diol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)CO NHEKBXPLFJSSBZ-UHFFFAOYSA-N 0.000 description 2
• NMSBTWLFBGNKON-UHFFFAOYSA-N 2-(2-hexadecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCO NMSBTWLFBGNKON-UHFFFAOYSA-N 0.000 description 2
• PVVTWNMXEHROIA-UHFFFAOYSA-N 2-(3-hydroxypropyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(CCCO)=NC(=O)C2=C1 PVVTWNMXEHROIA-UHFFFAOYSA-N 0.000 description 2
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• 229940035034 maltodextrin Drugs 0.000 description 1
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• DMMZYYLXAGRBDO-NSCUHMNNSA-N methyl (e)-4,4,4-trifluorobut-2-enoate Chemical compound COC(=O)\C=C\C(F)(F)F DMMZYYLXAGRBDO-NSCUHMNNSA-N 0.000 description 1
• VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 1
• JMKJCPUVEMZGEC-UHFFFAOYSA-N methyl 2,2,3,3,3-pentafluoropropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)F JMKJCPUVEMZGEC-UHFFFAOYSA-N 0.000 description 1
• MRPUVAKBXDBGJQ-UHFFFAOYSA-N methyl 2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)F MRPUVAKBXDBGJQ-UHFFFAOYSA-N 0.000 description 1
• JHROQORAJUWVCD-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JHROQORAJUWVCD-UHFFFAOYSA-N 0.000 description 1
• CJFAZQXPXXDAQR-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-henicosafluoroundecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CJFAZQXPXXDAQR-UHFFFAOYSA-N 0.000 description 1
• ABNZIVVYHQYSLI-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tricosafluorododecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ABNZIVVYHQYSLI-UHFFFAOYSA-N 0.000 description 1
• MCVGSSHSKHYZGK-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-pentacosafluorotridecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MCVGSSHSKHYZGK-UHFFFAOYSA-N 0.000 description 1
• DRRCLKOIEBNFIE-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-heptacosafluorotetradecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DRRCLKOIEBNFIE-UHFFFAOYSA-N 0.000 description 1
• QHUMNQRKSPEXJP-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,15-nonacosafluoropentadecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QHUMNQRKSPEXJP-UHFFFAOYSA-N 0.000 description 1
• YUFOZPVITJRTPY-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-pentatriacontafluorooctadecanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YUFOZPVITJRTPY-UHFFFAOYSA-N 0.000 description 1
• CFNCFMKWDPDIPT-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CFNCFMKWDPDIPT-UHFFFAOYSA-N 0.000 description 1
• XCSZRHBSQLYKOK-UHFFFAOYSA-N methyl 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-[1,1,2,3,3,3-hexafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]propoxy]propoxy]propanoate Chemical compound COC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F XCSZRHBSQLYKOK-UHFFFAOYSA-N 0.000 description 1
• CAWRUEZRLRNISR-UHFFFAOYSA-N methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate Chemical compound COC(=O)C(F)(OC)C(F)(F)F CAWRUEZRLRNISR-UHFFFAOYSA-N 0.000 description 1
• YPGCUXBNTDXTKF-UHFFFAOYSA-N methyl 2,3,3,3-tetrafluoropropanoate Chemical compound COC(=O)C(F)C(F)(F)F YPGCUXBNTDXTKF-UHFFFAOYSA-N 0.000 description 1
• LOYYAPWQNHOYQA-UHFFFAOYSA-N methyl 2,3,3-trifluoroprop-2-enoate Chemical compound COC(=O)C(F)=C(F)F LOYYAPWQNHOYQA-UHFFFAOYSA-N 0.000 description 1
• HTBBVKFFDDQVER-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC(Cl)=C1 HTBBVKFFDDQVER-UHFFFAOYSA-N 0.000 description 1
• CXZMJKWCYBWNTN-UHFFFAOYSA-N methyl 2-[[3-sulfanyl-2-[(2,2,2-trifluoroacetyl)amino]propanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C(CS)NC(=O)C(F)(F)F CXZMJKWCYBWNTN-UHFFFAOYSA-N 0.000 description 1
• QAOFGUXVDAZKBW-UHFFFAOYSA-N methyl 2-bromo-3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1Br QAOFGUXVDAZKBW-UHFFFAOYSA-N 0.000 description 1
• KLIFMERYWGSJJF-UHFFFAOYSA-N methyl 2-hydroxy-2-(trifluoromethyl)pent-4-enoate Chemical compound COC(=O)C(O)(C(F)(F)F)CC=C KLIFMERYWGSJJF-UHFFFAOYSA-N 0.000 description 1
• KSTORXDPAMPRFG-UHFFFAOYSA-N methyl 2-propoxypropanoate Chemical compound CCCOC(C)C(=O)OC KSTORXDPAMPRFG-UHFFFAOYSA-N 0.000 description 1
• XGLLQDIWQRQROJ-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-oxopropanoate Chemical compound COC(=O)C(=O)C(F)(F)F XGLLQDIWQRQROJ-UHFFFAOYSA-N 0.000 description 1
• FGGMNRZYEBHEIR-UHFFFAOYSA-N methyl 4,4,5,5,5-pentafluoro-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(F)(F)C(F)(F)F FGGMNRZYEBHEIR-UHFFFAOYSA-N 0.000 description 1
• QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
• 229960001664 mometasone Drugs 0.000 description 1
• QMCHYTVPUAJEMM-UHFFFAOYSA-N n-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-2,6-dimethyl-3-nitropyridin-4-amine Chemical compound CC1=NC(C)=CC(NCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1[N+]([O-])=O QMCHYTVPUAJEMM-UHFFFAOYSA-N 0.000 description 1
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 1
• RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 1
• 229960004398 nedocromil Drugs 0.000 description 1
• 230000008518 non respiratory effect Effects 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 230000036407 pain Effects 0.000 description 1
• WTWWXOGTJWMJHI-UHFFFAOYSA-N perflubron Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Br WTWWXOGTJWMJHI-UHFFFAOYSA-N 0.000 description 1
• 229960001217 perflubron Drugs 0.000 description 1
• 229950011087 perflunafene Drugs 0.000 description 1
• YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
• UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 1
• SIDINRCMMRKXGQ-UHFFFAOYSA-N perfluoroundecanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SIDINRCMMRKXGQ-UHFFFAOYSA-N 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
• 239000004810 polytetrafluoroethylene Substances 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• OUJAXDQRZMGUOM-UHFFFAOYSA-N prop-2-enyl 2,2,3,3,4,4,5,5,5-nonafluoropentanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OCC=C OUJAXDQRZMGUOM-UHFFFAOYSA-N 0.000 description 1
• DASVACNPTZCVQR-UHFFFAOYSA-N prop-2-enyl 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OCC=C DASVACNPTZCVQR-UHFFFAOYSA-N 0.000 description 1
• DNFFZVPOFBBNHH-UHFFFAOYSA-N prop-2-enyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OCC=C DNFFZVPOFBBNHH-UHFFFAOYSA-N 0.000 description 1
• ASAXRKSDVDALDT-UHFFFAOYSA-N propan-2-yl 2,2,2-trifluoroacetate Chemical compound CC(C)OC(=O)C(F)(F)F ASAXRKSDVDALDT-UHFFFAOYSA-N 0.000 description 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
• WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 description 1
• 229960002720 reproterol Drugs 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 description 1
• 229950004432 rofleponide Drugs 0.000 description 1
• 229960004017 salmeterol Drugs 0.000 description 1
• 238000012216 screening Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229940047670 sodium acrylate Drugs 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
• SCWLIHXXYXFUFV-UHFFFAOYSA-M sodium;2,2,3,3,3-pentafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)(F)F SCWLIHXXYXFUFV-UHFFFAOYSA-M 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000007790 solid phase Substances 0.000 description 1
• 230000007928 solubilization Effects 0.000 description 1
• 238000005063 solubilization Methods 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 238000012385 systemic delivery Methods 0.000 description 1
• IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
• UQJLSMYQBOJUGG-UHFFFAOYSA-N tert-butyl 2,2,2-trifluoroacetate Chemical compound CC(C)(C)OC(=O)C(F)(F)F UQJLSMYQBOJUGG-UHFFFAOYSA-N 0.000 description 1
• PIXVHVXDRVVEGH-UHFFFAOYSA-N tert-butyl 2,2,3,3,3-pentafluoropropanoate Chemical compound CC(C)(C)OC(=O)C(F)(F)C(F)(F)F PIXVHVXDRVVEGH-UHFFFAOYSA-N 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
• 229940110309 tiotropium Drugs 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 238000012549 training Methods 0.000 description 1
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
• 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
• 238000002255 vaccination Methods 0.000 description 1
• 239000013603 viral vector Substances 0.000 description 1
• 230000000007 visual effect Effects 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1